Lithium Hydroxide → (+/-)-2-(4-(8-Fluoro-2-oxo-1,2-dihydroquinazolin-3 (4H)-yl)piperidine-1-carboxamido)-3-(7-methyl-1H-indazol-5-yl)propanoic Acid

HRID 2099800Notes

Reaction equation

HRID 2099800 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([NH:21][CH:22]([CH2:27][C:28]3[CH:29]=[C:30]4[C:34](=[C:35]([CH3:37])[CH:36]=3)[NH:33][N:32]=[CH:31]4)[C:23]([O:25]C)=[O:24])=[O:20])[CH2:15][CH2:14]1)[CH2:7]2.O1CCCC1.CO.[OH-].[Li+]>O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]([NH:21][CH:22]([CH2:27][C:28]3[CH:29]=[C:30]4[C:34](=[C:35]([CH3:37])[CH:36]=3)[NH:33][N:32]=[CH:31]4)[C:23]([OH:25])=[O:24])=[O:20])[CH2:17][CH2:18]1)[CH2:7]2

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 11454987(+/-)-Methyl 2-(4-(8-fluoro-1,2-dihydro-2-oxoquinazolin-3(4H)-yl)piperidine-1-carboxamido)-3-(7-methyl-1H-indazol-5-yl)propanoateHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 57794659(+/-)-2-(4-(8-Fluoro-2-oxo-1,2-dihydroquinazolin-3 (4H)-yl)piperidine-1-carboxamido)-3-(7-methyl-1H-indazol-5-yl)propanoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of (±)-methyl 2-(4-(8-fluoro-1,2-dihydro-2-oxoquinazolin-3(4H)-yl)piperidine-1-carboxamido)-3-(7-methyl-1H-indazol-5-yl)propanoate (0.4 g, 0.79 mmol) in 1:1 tetrahydrofuran/methanol (30 mL) at room temperature was treated with a solution of lithium hydroxide (83 mg, 2.5 equiv) in water (4 mL) and stirred at room temperature overnight. The solvents were evaporated and the pH was adjusted to ca. 1 with 1 N hydrochloric acid. The resulting white suspension was stored at 4° C. overnight and the product was collected by filtration, washed with a small amount of water, and dried in vacuo to afford 0.21 g (74%) as a white powder. Mass spec.: 495.06 (MH)+.

Workup

  1. customThe solvents were evaporated
  2. waitThe resulting white suspension was stored at 4° C. overnight
  3. filtrationthe product was collected by filtration
  4. washwashed with a small amount of water
  5. customdried in vacuo
  6. customto afford 0.21 g (74%) as a white powder

Sources & evidence

ORD record
ord-4f7841e10a9b4155a480d05c7a37bf5b
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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